Smile Like Jack 5k/10k/Fun Run
- Date Sat 11th July 2026
- Time 9:00AM EDT
- Location East Otis, Massachusetts
- Price $38.10 - $43.40
- Races 3 races
- Distances 5km, 10km
Event summary
Get ready for a heartwarming day of fun and fitness at the fifth annual Smile Like Jack 5k/10k/Fun Run on Saturday, July 11, 2026, in the charming town of Otis, Berkshire! This vibrant event celebrates the spirit of Jack William O'Brien, a young man whose infectious smile and adventurous spirit inspired everyone around him. Participants can choose from a competitive 5k or 10k race, both chip-timed for those seeking a challenge, or join the Family Fun Run/Walk for a more relaxed experience.
Kick off the day with early check-in on Friday, July 10, from 4-7 PM at the Knox Trail Inn, or arrive bright and early on race day with check-in starting at 7 AM and the races launching at 9 AM. Enjoy delicious food, refreshing beverages (including 21+ options), exciting raffles, and uplifting music as you run or walk alongside fellow community members. Registration prices are $40 for the competitive races and $35 for the Family Fun Run/Walk. Don’t forget, the cutoff for T-shirt orders is June 1st! Rain or shine, this event promises to be a memorable day filled with smiles, camaraderie
Kick off the day with early check-in on Friday, July 10, from 4-7 PM at the Knox Trail Inn, or arrive bright and early on race day with check-in starting at 7 AM and the races launching at 9 AM. Enjoy delicious food, refreshing beverages (including 21+ options), exciting raffles, and uplifting music as you run or walk alongside fellow community members. Registration prices are $40 for the competitive races and $35 for the Family Fun Run/Walk. Don’t forget, the cutoff for T-shirt orders is June 1st! Rain or shine, this event promises to be a memorable day filled with smiles, camaraderie
Organiser's Description
Join us Saturday, 7/11/2026 for our FIFTH ANNUAL SMILE LIKE JACK FAMILY FUN RUN/WALK. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!
Early check-in will be held Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.
Day of registration and check-in begins promptly at 7:00 AM, while the race kickoff is at 9 AM.
Prices:
Competitive Race (Chipped Timed) 5k/10k
$40
Family Fun Run/Walk (Not Timed)
$35
We hope to see you there!
***Cutoff for T-shirts will be June 1st. This event is rain or shine!***
JACK'S STORY
The Smile Like Jack Memorial Fund was established in memory of Jack William OBrien, a loving son and brother, caring friend, and hard working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.
For additional information on THE SMILE LIKE JACK MEMORIAL FUND, and for live updates, please visit our website: https://smilelikejack.com
Early check-in will be held Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.
Day of registration and check-in begins promptly at 7:00 AM, while the race kickoff is at 9 AM.
Prices:
Competitive Race (Chipped Timed) 5k/10k
$40
Family Fun Run/Walk (Not Timed)
$35
We hope to see you there!
***Cutoff for T-shirts will be June 1st. This event is rain or shine!***
JACK'S STORY
The Smile Like Jack Memorial Fund was established in memory of Jack William OBrien, a loving son and brother, caring friend, and hard working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.
For additional information on THE SMILE LIKE JACK MEMORIAL FUND, and for live updates, please visit our website: https://smilelikejack.com
Races
-
5k
Incl. $3.40 Fee & T-Shirt
Sat 11th July 2026 (9:00AM EDT)
$43.40
CLOSED -
10k
Incl. $3.40 Fee & T-Shirt
Sat 11th July 2026 (9:00AM EDT)
$43.40
CLOSED -
Family Fun Run/Walk
Incl. $3.10 Fee & T-Shirt
Sat 11th July 2026 (9:00AM EDT)
$38.10
CLOSED
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The Knox Trail Inn, 1898 E Otis Rd, East Otis, 01029, MA, United States
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Smile Like Jack 5k/10k/Fun Run
